Methanol → HCID 18172424, compound

HRID 397070Notes

Reaction equation

HRID 397070 reaction equation
C([N:8]1[CH2:17][CH:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:15]2[C:10](=[CH:11][C:12]([O:26][CH3:27])=[CH:13][CH:14]=2)[CH2:9]1)C1C=CC=CC=1.CO.CCOC(C)=O>CCO.[Pd]>[CH3:27][O:26][C:12]1[CH:11]=[C:10]2[C:15]([CH:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH2:17][NH:8][CH2:9]2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 887Methanol2×HCID 8857Ethyl AcetateHCID 18172399HCID 18172399, compound

Product 1

HCID 18172424HCID 18172424, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 10% Pd/C (3.80 g) and 2-benzyl-7-methoxy-4-(4-methoxy-phenyl)-1,2,3,4-tetrahydroisoquinoline (3.87 g, 10.8 mmol, see Example 80) in EtOH (160 ml) was hydrogenated at 50 p.s.i. for 12 hours. The catalyst was removed via filtration through diatomaceous earth and the filtrate was concentrated in vacuo. Purification via flash chromatography (Biotage , SiO2, 9:1 EtOAc:MeOH then 1:1 EtOAc:MeOH) gave the title product (2.19 g, 8.13 mmol, 76% yield).

Workup

  1. customThe catalyst was removed via filtration through diatomaceous earth
  2. concentrationthe filtrate was concentrated in vacuo
  3. customPurification via flash chromatography (Biotage , SiO2, 9:1 EtOAc

Sources & evidence

ORD record
ord-0b380bb0a4934d9d9e1a6ef0dc8cf711
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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